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IMI'IIKNYLMKTIIANK                          2I3

It behaves towards ferric chloride and copper acetate like ethyl
acetoacetate (see Reactions, p. 84).
, ONa
I.                      CH,.C:   <)C.,ir-+ CH...CO.C,H.
()(', I -I,           "              "
- CH:,.C(C)N;i):CII.(X)'.CuTI. -f 2C2Hf,OH
en,.aY)Na):Cn.C<)C(;H- + C.,H,O,
- cii3.a) + Nac;H:jcx.
See Appcndi.\\ p. 309.
Dipheiiyliiiethane, C(l 11... C11._,. C(JI I.
Cohen, Hirst, Tnuts. Chan. S(n\: 1895, 67, 826.
60 grills. bcn/ene,
30          benzyl chloride.
I          aluminium-mercury couple.
The benzene is placed in a flask attached to an upright con-
denser.* The aluminium-mercury couple is then added. It is
prepared by pouring a saturated solution of mercuric chloride
on to aluminium foil, which is cut into strips or formed into rolls.
After about a minute, the surface of the aluminium is coated
with a film of metallic mercury. The solution is poured off, the
foil well washed with water, then with alcohol, and finally
with a little benxene. This must he done quickly and the
pieces of couple dropped into the benxene. The benzyl
chloride is added slowly from a tap-funnel inserted through
the lop of the condenser. A brisk effervescence occurs, accom-
panied by a considerable rise of temperature, and fumes of
hydrochloric acid are evolved. When, in. the course of an hour,
the benzyl chloride has been added, the flask is heated on the
water-bath for ten to fifteen minutes. The contents of the flask
are now shaken up with water containing a little caustic soda,
and the benxene solution separated in a tap-funnel. The
aqueous portion is again extracted with benxcnc, and the whole of
the'benzcne solution is dehydrated over calcium chloride. The
benxene is then distilled off, and when the thermometer reaches
iod' the distillation is continued /// wrae^. At 80 mm. cliphenyl-
methane boils at 174176'. This fraction solidifies completely